Method for selectively combating fungi and weeds

ABSTRACT

A method is provided for selectively and simultaneously controlling undesirable plant life in crop area wherein a culture of rice, potatoes, corn, beans, peas, soyabeans, cotton, peanuts, carrots or tomatoes are growing. According to the method of this invention an effective amount of the compound of the formula IS APPLIED TO THE CROP AREA.

nite Staes Martin et a1.

4 1 Sept. 19,1972

[54] METHOD FOR SELECTIVELY COMBATING FUNGI AND WEEDS [72] Inventors:'Henry Martin, Basel; Hans Aebi, Riechen; Ludwig Ebner, Stein/AG, all ofSwitzerland [63] Continuation of Ser. No. 766,308, Oct. 9,

1968, abandoned, which is a continuation-inpart of Ser. No. 592,747,Nov. 8, 1966, 'which is a continuation-in-part of Ser. Nos. 433,154,Feb. 16, 1965, abandoned, Ser. No. 433,152,

' Feb. 16, 1965, abandoned, Ser. No. 433,183, Feb. 16, 1965, abandoned,Ser. No. 433,204, Feb. 16, 1965, abandoned, Ser. No. 433,203, Feb. 16,1965, abandoned, Ser. No. 433,192, Feb. 16, 1965, abandoned, Ser. No.433,198, Feb. 16, 1965, abandoned, Ser. No. 433,153, Feb. 16, 1965,abandoned, each is a continuation-in-part of Ser. No. 191,442, May 1,1962, Pat. No. 3,288,851.

[30] Foreign Application Priority Data May 6, 1961 Switzerland ..5336/61[52] US. Cl ..424/322, 71/120 [51] Int. Cl. ..A0ln 9/20 [58] FieldofSearch ..71/120 [56] References Cited UNITED STATES PATENTS 3,079,2442/ 1963 Scherer et al ..71/120 3,165,549 l/1965 Martin et a1 ..71/120FOREIGN PATENTS OR APPLICATIONS 1,062,059 7/1959 Germany ..71/120Primary ExaminerJames 0. Thomas, Jr. Attorney-Harry Goldsmith, Joseph G.Kolodny, Bryant W. Brennan and Edward J. Sites [5 7] ABSTRACT is appliedto the crop area.

OCH;

1 Claim, No Drawings METHOD FOR SELECTIVELY COMBATING FUNGI AND WEEDSCROSS REFERENCE TO RELATED APPLICATIONS This application is acontinuation of application Ser. No. 766,308 filed Oct. 9, 1968, nowabandoned, which is a continuation in part of application Ser. No.592,747 filed Nov. 8, 1966 which is in turn a continuation in part ofapplications Ser. Nos. 433,154; 433,152; 433,183; 433,204; 433,203;433,192; 433,198; 433,153, filed Feb. 16, 1965, now abandoned which arein turn each a continuation in part of application Ser. No. 191,442filed May 1, 1962, now US Pat. No. 3,288,851.

BACKGROUND OF INVENTION This application relates to a novel method ofselectively controlling undesirable plant life especially both fungi andweeds in cultures of commercially valuable crops such as rice, potatoes,corn, beans, peas, soyabeans, cotton, peanuts, carrots and tomatoes.

As is well known to those skilled in the art the yield obtained in anarea planted with the above noted crops is dependent to a large extendon controlling weeds and fungi in the crop area. Certain compounds canbe employed which are herbicidally active. to control the weeds. Thecompounds employed as herbicides in a crop area must selectively controlthe growth of the weed but must not substantially affect the growth ofthe desired group. To control fungi it was suggested to use certainfungicidally active compounds. These compounds also have to be selectiveso as not to affect the desired crop. The requirement of employing botha herbicide and fungicide was not completely satisfactory. It requiredthe purchase and application of two different products. Furthermore eachproduct had to be separately evaluated to determine its affect on thedesired crop.

Various compounds of the prior art were suggested for use as total orselective herbicides. Typical of the compounds suggested for the use arethe urea derivatives such as those disclosed in US. Pat. No. 2,960,534which discloses the herbicidal compound of the formula OCH;

The above compound was indicated to have some selectivity with regard toherbicidal activity but it was not completely satisfactory because itdid not exhibit any fungicidal activity. Accordingly when the abovenoted prior art compound was employed in a crop area it had to beemployed together with another compound having fungicidal activity inorder to control both weeds and fungi.

It is an object of the invention to provide a method for simultaneouslyand selectively controlling both fungi and weeds in an area wherein acommercial valuable crop is grown.

It is a further object of this invention to provide a method forsimultaneously and selectively controlling both fungi and weeds in anarea wherein certain commercially valuable crops are grown in which onlyone active compound need be employed.

SUMMARY OF THE INVENTION A method is provided for pre-emergently orpostemergently selectively controlling fungi and weeds in an area wherecommercially valuable crops are grown in which a fungicidal weed killingamount of the compound of the formula 0 O C Ila is applied to the areain which the crop is planted.

DETAILED DESCRIPTION OF THE INVENTION The present invention is based onthe observation that the compound of the formula O OCH:

is very useful in selectively combating both fungi and weeds in aculture of potatoes, rice, corn, beans, soyabeans, peas, cotton peanuts,tomatoes or carrots.

Preparations are also provided for selectively combating weeds and fungiin a culture of said plants, which contain as an active ingredient thecompound of form ula (I) and an inert carrier or a solvent, a diluent,an emulsifier, a dispersing agent, a wetting agent, an adhesive agent, afertilizer, a bactericide, a nematocide, an insecticide or anotherselective herbicide or fungicide.

For preparing solutions containing the compound of the formula (I) whichare suitable for spraying as such there may be used, for example,organic solvents boiling above C, e.g. mineral oil fractions boilingabove 100 C, such as diesel oil or kerosene, or coal tar oils or oils ofvegetable or animal origin, or hydrocarbons, such as alkylatednaphthalenes, tetrahydronaphthalene, if desired, with the use of xylenemixtures, cyclohexanols, ketones, or

chlorinated hydrocarbons, such as tetrachlorethane, trichlorethylene ortrior tetra-chlorobenzenes.

As preparations that can be diluted with water to yield aqueous liquorsfor application as such there may be mentioned emulsion concentrates,pastes or wettable powders. As emulsifying or dispersing agent there areused nonionic products, such as condensation products of aliphaticalcohols, amines or carboxylic acids containing a hydrocarbon radicalhaving 10 to 30 carbon atoms with ethylene oxide, such as condensationproduct of octadecyl alcohol with 25 to 30 mols of ethylene oxide or ofsoya bean oil fatty acid with 30 mols of ethylene oxide or of commercialoleylamine with 15 mols of ethylene oxide or of dodecyl mercaptan with12 mols of ethylene oxide. As anionic emulsifying agents there may bementioned the sodium salt of dodecyl alcohol sulfuric acid ester, thesodium salt of dodecyl-benzene sulfonic acid, the potassium ortriethanolamine salt of oleic acid or of abietic acid or of a mixture ofthese acids, or the sodium salt of a petroleum sulfonic acid. Ascationic dispersing agents there may be used quaternary ammoniumcompounds, such as cetyl-pyridinium bromide ordihydroxy-ethyl-benzyldodecyl-ammonium chloride.

A solid carriers for making dusting or strewing powders there may beused talcum, kaolin, bentonite, calcium carbonate or calcium phosphate,or carbon cork meal or wood meal or other materials of vegetable origin.It is very advantageous to make up the preparations in a granulatedform. The preparations in their various forms may also have incorporatedtherewith in the usual manner substances that improve theirdispersibility, adhesion, resistance to rain or penetrating power, suchas fatty acids, resins, glue, casein or, for example, alginates.

The following Examples illustrate the invention, the parts being byweight.

EXAMPLE 1 27 grams of N-phenyl-N-methoxy-N'-methyl-urea are dissolved in100 cc of glacial acetic acid, l2.3 grams of anhydrous sodium acetateare added, and the bromination is carried out at 70 C with 26.3 grams Brdissolved in glacial acetic acid.

The yield of crude N-4 bromophenyl-N-methyl-N'- methoxy-urea is 34grams. The crude product melts at 9 1 to 94 C, and, when recrystallizedfrom cyclohexane, the product melts at 95 to 96 C.N-4-bromophenyl-N'-methyl-N-methoxy-urea obtained by a known method fromparaebromo phenyl isocyanate and ON- dimethyl-hydroxyl-amine melts at95.5 to 96 C. A mixture of the latter with the compound prepared asdescribed above melts at 945 to 95.5 C.

Analysis: C l-l N Br Calculated: C 41.72% H 4.28% Br 30.84% Found: C41.89% H 4.43% Br 30.61%

EXAMPLE 2 a. To l0 parts of the compound of the above formula (I) areadded 2 parts of sulfite cellulose waste liquor and 100 cc of water, andthe mixture is then subjected to intense grinding, to yield a stabledispersion of fine particle size which may be diluted as required withwater.

b. to 50 parts of the compound of the formula (I) are added 40 parts ofkaolin (Bolus alba), 3.5 parts of a condensation product of 1 mol ofpara-tertiary octylphenol with 8 mols of ethylene oxide, 15 parts ofheptadecenyl-benzimidazole sulfonate and parts of finely divided SiO themixture is then subjected to intense grinding, to yield a stabledispersion of fine particle size which may be diluted as required withwater.

EXAMPLE 3 a. An aqueous dilution of the dispersion according to Example2(b) was applied as a spray to a field planted with Irish potatoes(variety Red Pontiac) at the rates of 1.5 and 3 pounds of activesubstance per acre,

OCH;

2 days after the planting of the potatoes. The following weeds werepresent in the test field:

Common Name Scientific Name Goosegrass Eleusine indica CrabgrassDigitaria sanguinalis Pangolagrass Digitaria decumbens BermudagrassCynodon dactylon Bahiagrass Paspalum notatum Pokeweed Phytolaccaamericana.

At the weed evaluation 2 months after the treatment, all the weedspresent in the test field were completely or almost completely killed.There was no phytotoxicity observed on the potatoes treated. At theyield evaluation 3 months after the planting date there was observedthat the test field treated according to the invention yielded overone-third more potatoes than an untreated control field. Good selectiveherbicidal effects were also obtained according to the method describedin this Example with an application rate of 0.5 pound of activesubstance per acre.

b. In another test a culture of white potatoes was treated in the mannerset forth above under (a), the application rates being 1.0 and 3.0pounds of active substance per acre. There was observed at the weedevaluation 2 months after the treatment that the following weeds whichhad been predominant in the treated field were practically completelykilled:

Crabgrass, Ragweed (Ambrosia trifida), and Smartweed (Polygonum).

No phytotoxicity was observed on the potatoes treated.

c. In a further test an aqueous dilution of the dispersion according toExample 2 was applied as a spray to a field planted with white potatoes,at the rate of l.0 pound of active substance per acre, 4 weeks after theplanting of the potatoes. There was observed at the weed evaluation 1month after the treatment that the following weeds which had beenpredominant in the treated field were practically completely killed:

Foxtail, Ragweed and Smartweed.

No phytoxicity was observed on the potatoes treated, even if theapplication rate was raised up to 8 pounds of active substance per acre.d. Potatoes were planted in rows. Three days afterwards, the field wassprayed with a spraying liquor according to Example 2 (a), using 1.0,2.0 or 3.0 pounds of active substance per acre, respectively.

Results were evaluated 57 days after the treatment. The potatoes haddeveloped quite normally, whereas the weeds that had grown up to thetreatment date were killed practically completely, as is evident fromthe following Table (Red dead nettle) (Lambsquater 7 Ratings:

10 means full effect, plant absolutely dead.

means plant quite normal.

EXAMPLE 4 Aqueous dilutions of the dispersion according to Example 2 (b)were applied as sprays at rates decreasing from 8 to 0.25 pounds ofactive substance per acre to cultures of rice plants (paddy rice) in thefollowing manner:

1. Pre-plant soil incorporation. (Harrowed into the soil two days beforethe rice was sown) 2. Preemergent application. (Spraying of the field 1day after the sowing of the rice) Evaluation: in the case of l) 7 weeksafter the treatment in the case of (2) 7 weeks after the treatmentResults:

At the time of the evaluation an untreated control field was heavilyinfested with junglerice (Panicum) as the only weed present. In the caseof the test fields treated according to the methods l.) and (2.) setforth above, it was observed that at the rate of 0.5 pound per acre ofactive substance the rice cultures were completely freed from thejunglerice and that the rice tolerated 8.0 pounds per acre of activesubstance without being damaged.

EXAMPLE a. An aqueous dilution of the dispersion according to Example2(b) was applied as a spray to a field sown with corn at a rate of 0.5pounds of active substance per acre, 2 days after the sowing of thecorn.

At the weed evaluation, 4 weeks after the treatment,

it was observed that the following weeds which have been predominant inthe treated field, were completely killed: Lovegrass, Crabgrass andPigweed. There was no phytotoxicity observed on the treated corn. b.Aqueous dilutions of the dispersion according to Example 2 (b) wereapplied as sprays at rates decreasing from 8 to 2.0 pounds of activesubstance per acre to cultures of corn in the following manner:

1. pre-plant soil incorporation (Harrowed into the soil two days beforethe corn was sown).

2. pre-emergent application (spraying of the field 1 days after thesowing of the corn). Evaluation in both cases:

4 weeks after the treatment. Results:

At the time of the evaluation an untreated control field was heavilyinfested with junglerice (Panicum) as the only weed present. in the caseof the test fields treated according to the methods (1) and (2) setforth above, it was observed that at rates of 2.0 pounds per acre ofactive substance the corn cultures were completely freed from thejunglerice and that the corn tolerated 8.0 pounds per acre of activesubstance without being damaged. c. A field was sown with corn andtreated 1 day thereafter with an aqueous dilution of the dispersion setforth in Example 2(a) at a rate of 2.0 pounds of active substance peracre.

Examination four weeks after the treatment revealed that the followingweeds were killed completely: Senecio vulgaris (Birdweed), Chenopodiumalbum Lambsquater), Sonchus ole raceus (Perenniol sowthistle), Lamiumpurpureum (Red dead nettle), Sinapis arvensis (Wild mustard), Matricariachamomilla (chamopulle), Stellaria media (chickweed). The corn plantssuffered no harm from this treatment.

EXAMPLE 6 a. An aqueous dilution of the dispersion according to Example2(b) was applied as a spray to two test fields sown with Lima beans andSoybeans, respectively at a rate of 0.5 pounds of active substance peracre, 2 days after the sowing of said plants.

At the weed evaluation, 4 weeks after the treatment,

it was observed that the following weeds which had been predominant inthe treated fields, were completely killed: Lovegrass, Crabgrass andPigweed. There was no phytotoxicity observed on the treated crop plants.b. Aqueous dilutions of the dispersion according to Example 2(b) wereapplied as sprays at rates decreasing from 8 to 2.0 pounds of activesubstance per acre to cultures of beans (Wade" variety), peas (purpleHull 49 variety), and soybeans (Clemson variety) in the followingmanner:

1. pre-plant soil incorporation: (Harowed into the soil two days beforethe crop lants were sown).

2. pre-emergent application: (spraying of the field l day after thesowing of the corps).

Evaluation in both cases: 4 weeks after treatment. Results:

At the time of the evaluation an untreated control field was heavilyinfested with junglerice (Panicum) as the only weed present. In the caseof the test fields treated according to the methods (1) and (2) setforth above, it was observed that at the rate of 2.0 pounds per acre ofactive substance each of the three grop cultures was completely freedfrom the junglerice; beans and the peas tolerated 8.0 pounds, and thesoybeans tolerated 14.0 pounds per acre of active substance withoutbeing damaged.

c. In a further pre-emergent test there was achieved a full effectagainst seedling of Johnson grass, sedge, and whiteclover growing in aculture of soybeans; the application rate of the active principle of thedispersion according to Example 2(b) was 2.0 pounds per acre; no damageto the soybeans could be observed.

d. A field was sown with dwarf beans and treated 1 day later (field A)or 9 days later (field B) with the spray liquor described in Example(2a) at the rates of 0.75 and 1.5 pounds per acre, respectively.

At the time of the A-treatment, neither weeds nor beans had germinated.At the time of the B-treatment the weeds were in cotolyden stage. Thebeans had just emerged from the soil, their cotolydens had not unfolded.Four weeks after the treatment, the results were evaluated, and areshown in the Table below.

Sonchus asper (Spring sowthisthle l l0 l0 I0 I Chenopod. alb. l0 l0 l0 l(Lampsquater Stellaria media l0 l0 l0 l0 1 (chickweed) Capsella b.past.I0 10 l0 I0 I (Shepherd's purse) Sinapis arvens. 8 l0 l0 10 l (Wildmustard) Veronica persic. l0 l0 l0 I0 I (Buxbaums speed well) Polygonumconvulvulus 2 7 l0 10 l (birdweed) Ratings:

10 means full effect plant absolutely dead 0 means plant quite normal.The beans had suffered no harm whatever from this I treatment.

EXAMPLE 7 a. An aqueous dilution of the dispersion according to Example2(b) was applied as a spray to a field sown with cotton at a. rate of0.5 pounds of active substance per acre, 2 days after the sowing ofcotton plants.

At the weed evaluation, 4 weeks after the treatment, it was observedthat the following weeds which had been predominant in the treatedfield, were completely killed: Lovegrass, Crabgrass and Pigweed. Therewas no phytotoxicity observed on the treated cotton plants. b. Aqueousdilutions of the dispersion according to Example 2(b) were applied assprays at rates decreasing from 4 to 2 pounds of active substance peracre to cultures of cotton plants in the following manner:

1. pre-plant soil incorporation (Harrowed into the soil two days beforethe cotton was sown).

2. pre-emergent application (spraying of the field l day after thesowing of the cotton). Evaluation in both cases:

4 weeks after the treatment. Results:

At the time of the evaluation an untreated control field was heavilyinfested with junglerice (Panicum) as the only weed present. In the caseof the test fields treated according to the methods l) and (2) set forthabove, it was observed that at rates of 2.0 pounds per acre of activesubstance the cotton cultures were completely freed from the junglericeand that the cotton tolerated 4.0 pounds per acre of active substancewithout being damaged.

c. In a special tolerance test wherein an aqueous dilution of thedispersion according to Example 2(b) was employed, it was observed thatunder the conditions set forth above under b. the cotton plantstolerated up to 8.0 pounds of active substance without being damaged.

EXAMPLE 8 a. An aqueous dilution of the dispersion according to Example2(b) was applied as a spray to a field sown with peanuts at a rate of0.5 pounds of active substance per acre, 2 days after the sowing ofpeanuts.

At the weed evaluation, 4 weeks after the treatment, it was observedthat the following weeds which had been predominant in the treatedfield, were completely killed: Lovegrass, Crabgrass and Pigweed. Therewas field, phytotoxicity observed on the treated peanut culture.

b. Aqueous dilutions of the dispersion according to Example 2( b) wereapplied as sprays at rates decreasing from 8 to 2 pounds of activesubstance per acre to cultures of peanuts in the following manner:

I. pre-plant soil incorporation (Harrowed into the soil two days beforethe peanuts were sown).

2. pre-emergent application (Spraying of the field l day after thesowing of the peanuts). Evaluation in both cases:

4 weeks after the treatment. Results:

At the time of the evaluation an untreated control field was heavilyinfested with junglerice (Panicum) as the only weed present. In the caseof the test fields treating according to the methods l) and (2) setforth above, it was observed that at rates of 2.0 pounds per acre ofactive substance the peanut cultures were completely freed from thejunglerice and that the peanuts tolerated 8.0 pounds per acre of activesubstance without being damaged. 0. In a further pre-soil applicationtest wherein an aq ueous dilution of the dispersion according to Example2(b) was applied at a rate of 1.0 pound of active substance per acre,the following previously predominant weeds were completely killed: dock,whiteclover and pepperweed. The peanuts tolerated 8.0 pounds of activesubstance without being damaged.

EXAMPLE 9 a. Aqueous dilutions of the dispersion according to Example2(b) were applied as sprays at rates decreasing from 4 to 1 pound ofactive substance per acre by preplant soil incorporation (I-Iarrowedinto the soil two days before the tomatoes were planted).

At the evaluation 4 weeks after the treatment of the soil it wasobserved that the following weeds present in the cultures were killed asa result of active substance per acre: Dock, whiteclover and pepperweed.The tomatoes tolerated up to 8.0 pounds of active substance per acre,without being damaged.

b. In a further test aqueous dilutions of the dispersion according toExample 2(b) were applied as sprays to tomato cultures 1 day after theplanting of the crops.

At the evaluation 4 weeks after the treatment, it was observed that at arate of 0.5 pounds of active substance per acre the following weeds werekilled: Dock and whiteclover, and that at a rate of 2.0 pounds of activesubstance per acre the following weeds were killed: sedge and seedlingJohnson grass. No phytotoxic effects on the treated tomatoes wereobserved.

0. In a further test tomato plant were sprayed with an aqueousdispersion of the composition prepared in Example 2(b). The dispersionapplied in an amount equivalent to 2 pounds per acre. Two days afterspraying the plants were infested with a spore suspension ofPhytophthora infestans. After infestion the plants were held for 2 daysin an incubation chamber at l00% relative humidity and 2225 C. Thefollowing results were obtained 6-8 days after infection. The resultsare compared with tomato plats subjected to the same treatment exceptfor the treatment with the compound of this invention. The untreatedplant were infested with the fungi while the treated plant were free ofinfestation.

d. The procedure described in Example 9(c) was repeated with theexception that the soil was infested with dock, whiteclover andpepperweed. After 4 weeks the culture was examined and found to be freeof both fungi and weed while the tomato plants did not appear to beaffected.

EXAMPLE l Aqueous dilutions of the dispersion according to Ex ample 2(b)were applied as sprays at rates of 0.75 and 1.5 pounds of activesubstance per acre to cultures of carrots, 2 weeks after the corps hadbeen sown. At the evaluation 4 weeks after the treatment, it wasobserved that the following weeds which had been predominant in thetreated test field, were practically completely killed: Lambsquater,Ragweed and Smartweed. No phytotoxic effects on the treated carrots wereob served.

In a tolerance test it was observed that the carrots tolerated 6 poundsof active substance per acre in case of preemergent application and inthe case of postemergent application.

EXAMPLE 1 l The compound of formula (I) was very active against harmfulnematodes, e.g. panagrellus redivivus, when applied, for instance, at arate of 0.01% by weight.

EXAMPLE 12 A percent aqueous solution was mixed with/percent by weightpropylene glycol solution of the compound prepared in Example 1.

Three solutions were prepared one having 600 PPM, a second having 500PPm and a third having 250 PPM of the active compound prepared inExample one.

The resulting solution were inoculated with 1 drop of a spore suspensionof Rhizopus Nigricans and incubated for 4 days at 24 C whereafter thefungicidal effeet was checked by determining the growth of the myceliumand comparing it with a control containing no active compound but thesame amount of nutrient medium as the test sample Concentration activecompound Result 600 PPM fungicidal activity 500 PPM as above 250 PPM asabove CONTROL no apparent fungicidal activity EXAMPLE 13 O 0 CH3

